We all know we’re supposed to have one-on-one (1:1) meetings with our direct reports. But the value managers and employees get from them is… sadly inconsistent. Here’s how I wrangled my 1:1s so they could be predictable, useful, and leave us both feeling better about the work ahead of us.

And lest you think I’m some sort of 1:1 genius, this is the result of advice I cobbled together from peers and experts (Lara Hogan and Paloma Medina, in particular).

One on ones (1:1s) are the place where you as a manager have the most to gain and the most to give. Yeah, there are bigger review cycles where you can hopefully get the people on your team the pay and titles they deserve, but 1:1s are small and regular enough that they make the biggest difference overall. 1:1s are basically the stream steadily wearing its way through rock until you have a national park or something.

Regular 1:1s

Predictability is important when you have regular recurring meetings. A one hour meeting without an agenda is a terrifying prospect - are you going to be expected to talk at length about something you haven’t been focusing on? Is it going to be a total waste of time? How many capybara videos is it going to take to bring my blood pressure down afterwards?

That’s why I like to use the exact same questions every time (it’s also easier than reinventing the wheel each time). So here are my 1:1 questions:

  1. What’s the most important thing we talk about today?
  2. Follow ups from previous meetings/things that came up this week.
  3. What are your wins?
  4. What are your worries?
  5. Org updates
  6. Weird Manager Questions

The most important thing

After the standard “hello, how are you” style greetings (you’ll probably notice some people need to have more or less of the pleasantries) the first question for me is always “What is the most important thing that we talk about today?” The first time you ask this is usually moderately bewildering to employees, who have probably grown used to managers just telling, not hearing. If their answer is “I don’t know?” or “I’m doing fine, actually, what do you think is most important?” that’s groovy! But by always asking this question, they come to really internalize that this is THEIR meeting, and they can cover the things that make them happier at the company for longer.

Follow ups

If you discussed anything last time that requires follow up, do that next. Actually following up on the things that matter to your employee is the number one way to make them feel valued and like positive change is possible. Keeping your 1:1 notes in Clickety will make tracking those easy.


“What are your wins for the past week?” allows your employee to tell you what is fueling them. Often these wins will be project-focused. Sometimes it will be about how the team handled a crisis well. Sometimes they won’t be able to think of one and you need to go into triage mode immediately. But asking that every week and writing the answers down allows you to quickly find things to call out when review/promo cycles roll around, and also will be very handy for your employee when they need to refresh their resume. You should tell them that, too. It shows that you are invested in them. Yeah, it’d be great if we all stayed on the team forever, but we know that’s not realistic any more, so we really should stop pretending that talking about ever leaving is taboo.


“What are your worries?” is a chance for them to bring up a project that might be going off the rails, or prickly interpersonal dynamics. Capturing these allows for you to quickly track the evolution of issues over time if they are long-running. This question also opens the door for employees who have been trained to never complain about things to voice their concerns in a way that “What’s the most important thing that we talk about today?” might not necessarily invite.


Next up is org updates. As a manager, you’re constantly told “make sure your employees are aware of this and/or that,” “remind them to respond to this survey,” or “no, for real, open enrollment ends Friday.” Or maybe you don’t even get the benefit of being told what they should be made aware of and you just have to pluck out of the air the things they will need to know (it can be a thankless job, do you need some capybara videos?). I’ll also add to that major changes the company rolled out if I think it may impact my team (e.g. “so how are you feeling about that reorg?"). I want to know if changes like that are eroding the trust my team has in me and the company so that I can raise concerns up and try to mitigate stress down.

I keep a list of org updates on a sticky note for each 1:1 cycle to make sure I’m giving the same updates to everyone on the team.

Once that’s done, if there are any questions you have about projects/work deliverables, you should ask them here, but it is better for regular project updates to be done asynchronously through other tools like email or updated tickets.

Weird Manager Questions

If there’s time after going over all these, I’ll say “That’s my list - do you want time back, or to chat about anything else, or are you interested in a weird manager question?”. But what is a weird manager question, you ask? You know how you can read a management blog (like this one) and get inspired and want to try it out, but it might feel too… I think my dad would call it hippy-dippy. This is time for those kinds of questions or exercises. I’ll make a collection of them later, but may I recommend:

  • “Think about how you spend your time at work. Divide this sticky note/whiteboard square/drawing doc into the different things you do. Are these the right amounts of time you should/want to be spending on each of these? What would an ideal distribution of your time look like?”
  • “What ways can we show you we appreciate what you do?”
  • “Using Paloma Medina’s BICEPS framework, how are you doing across each of your core needs?” I like to use a scale model and track this over time. You can use something like “On a scale of 1 to 5, where 1 is ‘I feel awful’ and 5 is ‘happy as a clam,’ where are you on Belonging?” or something more tactile like “Here’s an empty battery outline - how ‘full’ or ‘empty’ are you feeling on Predictability?”

Record Keeping

Keeping records of what you’ve talked about is important - particularly with issues that impact employees. These notes to be easy/small enough that you will actually take them and accessible enough that you can extract the relevant data when needed. Clickety allows you to create manual activities which are great for recording what you discussed in a meeting. Not only can you flag those for following up, you can search and find the first time an employee mentioned conflict with another team or concern over a deadline.

1:1 notes in new activity field

Follow ups

If you use manual activities to record your 1:1 notes, you can mark those interactions with follow ups; if you take pretty lengthy notes, throw an asterisk in front of the item that needs to be brought back up next time. If you can afford a minute before each meeting to extract those follow ups from your previous note and add them to your new 1:1 notes, it’s easy to say something like “Last week we talked about how to work better with the QA team - how did that conversation go?”. This looks friggin’ smooth. You have such a big brain that you remembered what happened last time? Dang, you must be a great manager.

Email notes

If you have the capacity, some managers send their employees a wrap-up email with their notes after each 1:1. This creates a trail not just for you, but also for your employee (so be sure to include their wins each time). If there are follow up items, you can bcc folllowup@clickety.email and it will show up as a follow up in Clickety (FYI, this isn’t a real email - Clickety just sees that you sent something to that address and adds the follow up flag).

“First” 1:1s & Capturing Human Context

Even if you’ve been meeting with someone for a while, you can use these questions as “weird manager questions” at any point - I’d even recommend revisiting them periodically, as preferences shift and employees grow (I particularly like revisiting these around the new year).

The first time you have a 1:1, you are establishing a relationship. Even if you already knew this person, the fact that you are now in a manager position changes that relationship. Don’t try to ignore it. Own it.

Your first 1:1 is about establishing ground rules. You should establish things like how long a 1:1 needs to last, how frequent they will be, and what to expect. You’ll also want to ask questions like how they prefer to receive constructive feedback and how they like to receive praise. Document these for easy reference (the Notes section on a Clickety person’s card is perfect for this!). I prefer to use emoji for each section so that scanning for this information is easier.

These are my questions (and emoji) that I go over in the first 1:1

  • πŸ“ˆ How do you like to receive constructive feedback? Immediately/ad hoc? Or should I save it up and tell you in our 1:1s? Do you prefer written in email? Slack? Or do you want to be able to discuss it over a call?
  • πŸŽ‰ How do you like to receive praise? Sometimes I phrase this as “what is your work love language? What things can I do that will meaningfully show you you are appreciated and we want you here?” This might be public shout outs at an all hands (or that may be the absolute LAST thing they ever want). Maybe they will feel appreciated by getting gift cards or an afternoon off or by sending a regular trickle of capybara videos.
  • β˜€οΈ What are the work areas that excite you most? In the roles I’ve had, there is often a broad scope of work that individual contributors cover, so knowing who prefers to do what helps keep folks happy.
  • πŸ”₯What things burn you out? This might be “never put me in charge of documentation.” It might be “Please don’t tell me how to do something, just point me at the problem or I’ll feel stifled.” It might be “boredom.” Basically, people are going to answer this question with their most open wounds. Pay attention, because repairing burn out is extremely difficult. Related: “How will I know you are burning out?”

The answers to these questions are fundamental to working well with each other, so I like to have them visible at every 1:1 I have. With Clickety, I can add each person’s answers to their notes field.

notes field with sample data

I hope these tips are helpful! If you have other great ideas and recommendations, we’d love to hear about them on LinkedIn, Twitter, or Facebook! And if you’d like to try out Clickety for running your 1:1s, sign up for the waitlist below!